2-(Diphenylphosphino)benzaldehyde

Base Information

• Chemical Name: 2-(Diphenylphosphino)benzaldehyde
• CAS No.: 50777-76-9
• Molecular Formula: C19H15OP
• Molecular Weight: 290.301
• Hs Code.: 29310099
• European Community (EC) Number: 627-711-4
• UNII: 5M9BQ2FEC8
• DSSTox Substance ID: DTXSID50373019
• Nikkaji Number: J617.981I
• Wikipedia: 2-Diphenylphosphinobenzaldehyde
• Wikidata: Q4596874
• Mol file: 50777-76-9.mol

Synonyms:2-(Diphenylphosphino)benzaldehyde;50777-76-9;2-Diphenylphosphinobenzaldehyde;2-diphenylphosphanylbenzaldehyde;Benzaldehyde, 2-(diphenylphosphino)-;o-(Diphenylphosphino)benzaldehyde;(2-Formylphenyl)diphenylphosphine;5M9BQ2FEC8;MFCD00013367;2- diphenylphosphino formaldehyde;2-(diphenylphosphanyl)benzaldehyde;UNII-5M9BQ2FEC8;o-Diphenylphosphinobenzaldehyde;SCHEMBL705407;2-Formylphenyldiphenylphosphine;SCHEMBL8464217;DTXSID50373019;DRCPJRZHAJMWOU-UHFFFAOYSA-N;AMY39359;BCP05529;AKOS004909029;CS-W014553;GC10227;2-(Diphenylphosphino)benzaldehyde, 97%;AS-14898;BP-12624;SY029813;D4411;FT-0639943;EN300-7386263;A828295;J-506400;Q4596874;Z3018592683;(2-Formylphenyl)diphenylphosphine, o-(Diphenylphosphino)benzaldehyde;(2-FORMYLPHENYL)DIPHENYLPHOSPHINE;2-(DIPHENYLPHOSPHINO)BENZALDEHYDE;DPPBDE;O-(DIPHENYLPHOSPHINO)BENZALDEHYDE

Chemical Property of 2-(Diphenylphosphino)benzaldehyde

Chemical Property:

• Melting Point: 112-115 °C(lit.)
• Boiling Point: 417.444 °C at 760 mmHg
• Flash Point: 206.263 °C
• PSA: 30.66000
• LogP: 3.25730
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 290.086052095
• Heavy Atom Count: 21
• Complexity: 300

Purity/Quality:

99.9% ^*data from raw suppliers

2-Diphenylphosphinobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3C=O
• Uses: suzuki reaction

Technology Process of 2-(Diphenylphosphino)benzaldehyde

There total 25 articles about 2-(Diphenylphosphino)benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

N,N-diethyl 2-diphenylphosphinobenzamide (143024-49-1) → (2-formylphenyl)(diphenyl)phosphine (50777-76-9)

Guidance literature:

With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 20 ℃; for 0.0333333h; Inert atmosphere;

DOI:10.1021/ol403183a

Reference yield: 85.0%

ortho-bromobenzaldehyde (6630-33-7) + diphenylphosphane (829-85-6) → (2-formylphenyl)(diphenyl)phosphine (50777-76-9)

Guidance literature:

With triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 2h; Heating;

DOI:10.1002/1615-4169(200108)343:6/7<711::aid-adsc711>3.3.co;2-t

Reference yield: 85.0%

2-(ortho-diphenylphosphinophenyl)-1,3-dioxolane (50777-73-6) → (2-formylphenyl)(diphenyl)phosphine (50777-76-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 8h; Reflux;

DOI:10.1039/c0dt01612h

upstream raw materials:

2-(diphenylphosphinoyl)benzaldehyde

2-(ortho-diphenylphosphinophenyl)-1,3-dioxolane

ortho-bromobenzaldehyde

diphenylphosphane

Downstream raw materials:

o-(Ph₂P)C₆H₄-CH=N-n-Pr

((2-hydroxymethyl)phenyl)diphenylphosphine

2-(diphenylphosphanyl)benzaldehyde oxime

N-[2-(diphenylphosphanyl)benzylidene]-N-ethylamine

Refernces

Hemilabile imino-phosphine palladium(II) complexes: Synthesis, molecular structure, and evaluation in Heck reactions

10.2478/s11696-013-0530-6

The research focuses on the synthesis, molecular structure, and evaluation of hemilabile imino-phosphine palladium(II) complexes in Heck reactions. The ligands 2-(diphenylphosphino)benzyl-(2-thiophene)methylimine (V) and 2-(diphenylphosphino)benzyl-(2-thiophene)ethylimine (VI) were prepared from 2-(diphenylphosphino)benzaldehyde and thiophene amines with high yields. These ligands were then reacted with PdCl2(cod) or PdClMe(cod) to form palladium(II) complexes I–IV. The molecular structure of complex II was confirmed by X-ray crystallography, revealing a distorted square planar geometry around the palladium atom. The complexes were evaluated as catalysts for the Heck coupling reactions of iodobenzene with methyl acrylate under mild conditions, showing significant activities with isolated yields of 64%, 68%, and 58% for complexes I, II, and IV, respectively. The study highlights the role of imino-phosphine ligands in enhancing catalytic activities due to their hemilabile property, which allows reversible protection of the coordination site.